


My Special Gangster

by thegreatficmaster



Series: Supernatural Collection [50]
Category: Supernatural
Genre: Angst, Character Death, Fluff, M/M, Murder, Reader-Insert
Language: English
Status: Completed
Published: 2019-07-18
Updated: 2019-07-18
Packaged: 2020-07-07 19:30:25
Rating: Teen And Up Audiences
Warnings: Major Character Death
Chapters: 1
Words: 1,715
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19856842
Author URL: https://archiveofourown.org/users/thegreatficmaster/pseuds/thegreatficmaster
Summary: Y/n moves to a small town, hoping he can get a fresh start, not knowing this is the home of gangster Dean Winchester.





	My Special Gangster

Y/n had no idea, when he moved to the little town, that this was the base of notorious gangster, Dean Winchester.

He’d heard of the man, killing his father to take over his criminal empire. 

His brother as his right hand man.

Castiel Novak, the devil himself, as his other.

He’d never even seen them. 

No one had. 

No one except the detective, Crowley. 

But he had long since died, shot in front of the station, his partner Lucifer being splattered with his blood.

Although y/n had nothing to do with this world, he was a very easily frightened man, deciding maybe it would be better to move to a small town instead of a huge city, thinking this would be safer.

The town was strange. 

Very strange. 

People seemed to always be on edge, making sure they didn’t say the wrong thing. 

They were all shady too.

Y/n had no idea what was happening in the town. 

All he knew was, he had a bad feeling.

He walked into the little speakeasy. 

He knew he shouldn’t be here. 

But he needed a drink. 

His family had disowned him. His friends hated him. And he knew no one in this town.

Walking in, he heard the ramblings of all the drunken people, smelling the alcohol and cigarettes.

Fuck, he desperately needed a drink.

Sitting at the bar, he ordered himself a drink, gulping it down and loving the burn it gave, missing the feeling.

He drank a few more, looking around and seeing a few of his neighbours in here, some people he’d seen around on the streets. 

They were having the time of their lives, dancing and drinking, enjoying the buzz that came not only from the alcohol, but the risk of getting caught.

The man in the booth in the corner caught his eyes. 

He was handsome. Very handsome. 

The suit he was wearing fit perfectly, showing off his broad chest and shoulders, his eyes dark and bright green, smoking a cigar and looking like the most beautiful man there was.

The stranger looked up, the men catching each other’s eyes.

Y/n quickly looked away. 

He couldn’t have anyone know he liked men. 

Not again. 

He didn’t want to be chased out of town, or worse.

He continued drinking, the buzz going to his head as he began loosening up. 

Not too much, just in case he did something he’d regret.

“Might wanna take it easy there”.

He looked to his left, seeing the attractive stranger sat on the stool next to him.

“And who might you be?”

“Dean. Dean Smith”, he answered, shaking the man’s hand.

“Nice to meet you, Dean. Y/n y/l/n”.

The man smiled at y/n, continuing the conversation, asking y/n where he was from and why he moved here.

Y/n didn’t tell the entire truth, knowing that wouldn’t be all that wise.

They spoke for a while longer, y/n laughing at Dean’s joke, all the patrons watching as the new guy spoke to the most notorious man in the state. 

Hell, the entire country.

“I mean, if it’s really a prohibition, why the hell am I able to get it in so easily?”

Y/n chuckled, placing his hand on Dean’s arm.

“Listen, no one wants this. Not really. They probably just let it in. At least that way, there’s a source of alcohol for them when their wives argue with them because they realize their husbands are all a complete waste of space”.

Dean nodded along, smiling at the man, his arm tingling from where y/n was still holding onto him.

“Anyyywaaaayy. I need to go to the home I live in. House. House, sorry. House? Or home? I don’t know”, he rambled on, the alcohol making his brain all jumbled.

He slid off his stool, his knees weak as he almost fell to the floor, the man in front of him catching him quickly.

“Thank you, good sir”, he said, tipping his hat and stumbling out of the little building, sneaking out and waddling down the road, his co-ordination poor.

He made it a few blocks, a voice making him turn.

“Might wanna get off the road”.

He stopped, looking down, before looking back at Dean.

“Whoopsie, my bad”, he chuckled, stumbling back onto the pavement.

Dean walked him home, the few people out watching as the man who ran the town accompanied the new guy, making sure to remember not to mess with him.

Y/n and Dean hit it off, the man often going over to the huge mansion, the largest house in the town, almost every day.

They kept it all private of course, not wanting people to know about it, just in case.

“Hey, y/n. Can you come with me?”

Y/n nodded, getting into the car with Dean and observing as the roads passed and houses blurred. 

He had no idea where Dean had led him, the little warehouse completely hidden away from the town.

Dean slid the door open, revealing a collection of alcohol and guns.

Y/n just stared at the guns, mainly tommy guns, a few shotguns and rifles.

“Wh-what is all this?”

Dean walked carefully towards y/n, seeing the frightened look in his eyes.

“It’s-I-ok. So, you know how I told you my name is Dean Smith?”

Y/n nodded, keeping at least five feet away from Dean.

“Well. That was a lie. My name is Dean. But not Dean Smith. It’s Dean Winchester”.

Y/n attempted to run out as soon as he realized just who this was.

“Wait, please. Don’t leave me”.

Y/n turned when he heard Dean’s voice cracking.

“I-I need you. I’ve never had someone love me like you. Please don’t leave me”.

Y/n debated it. 

On one hand, this was Dean Winchester, the gangster known everywhere. 

The one that was feared even by the cops. 

But on the other hand, he was Dean. 

The man he fell in love with in a matter of months.

He had come here to get away from the gangsters, not begin secretly dating one of the most notorious ones.

He sighed, resigning himself, knowing there was no way he could imagine himself without Dean. 

Sure, it was hard, keeping this all a secret, making sure no one found that the two men were together. 

But it was worth it.

They became stronger than ever, y/n not getting involved in Dean’s business, but the fact that he knew made it a lot easier, Dean not having to keep secrets from him.

Sam had a feeling, studying his brother’s shift in demeanour when y/n was around. 

He changed from the heartless man he had grown up with, the one who killed their own father by beating him to death with a bat wrapped in barbed wire.

Now, he was happier. 

He smiled more. 

Really smiled. 

He laughed, joked and didn’t get angry at the tailors for getting his measurements wrong.

But that just gave Sam something to hold against his brother.

He walked into Dean’s office one day, y/n sat on the couch as Dean sat at his desk, talking and laughing, the glimmer in each other’s eyes noticeable, confirming what Sam was suspecting.

“So, I want control of everything. And I want you gone. Now”, Sam demanded, Cas behind him, watching, having seen the look on Sam’s face when he walked in.

“What?”

“You think I haven’t noticed? How do you think people would feel, knowing the great Dean Winchester, is bedding another man?”

Dean’s eyes widened with rage, y/n’s heart thumping, thinking now he would have to leave.

“You don’t tell me what to do. What happens between me and y/n is none of your business. I am in control of everything. Not you”.

Sam scoffed, staring at y/n and Dean.

“Please. They’ll run you out of the town. Out of the state. Hell, out of the country. You really think people will want to do business with you when they know this?”

Before Sam could say another word, Dean pulled out a gun and shot his brother through the head, splattering the walls and Cas with blood.

Y/n jumped in shock, his hands clasped around his mouth.

“You don’t speak a word of this. Is that understood? Y/n will be left out of everything. You make sure he’s safe at all times. And don’t you dare say anything to him.”

Castiel nodded, not wanting to have the same thing happen to him.

Hell, he was a little happy. 

Sam Winchester was the worst person there was. 

He was even worse than Dean. 

It helped that now that Sam was gone, he was the second in command.

“Clean the mess up. Y/n, let’s go out to dinner”.

Y/n was still in shock, this being the first time he’d ever seen someone die in front of him.

Dean knelt down, his hands cupping y/n’s face as he looked him in the eyes.

“It’s ok. I promise”.

Y/n snapped out of his haze, looking back at Dean and smiling.

“Yea, let’s go”.

They left Cas to clean up the body, going out to dinner.

It didn’t take long for y/n to be pulled into the business, taking control over it all, Dean as his right hand, Cas, his other lover, helping too.

Eventually, the whole town knew about the relationship the three shared. 

But they wouldn’t do anything at all.

They’d seen the way y/n lost it, the now hardened man swinging the bat Dean killed his father with, smashing the man’s head open and smiling at his handiwork.

Dean didn’t know how to react. 

He was happy that y/n had been so taken with his work, learning it all himself and becoming even better at it than he was. 

But he hated that the once innocent man who knew nothing about this world, was now completely heartless. 

Well, to everyone except the two men he loved.

But Dean wouldn’t dwell on it too much. 

He was happy. 

He had his y/n, his Castiel, and the empire the three ran, becoming the most notorious gangsters in history.


End file.
